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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Southwest Side apartments

Games room

1. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A living room with a grey sofa, two chairs, a coffee table, and a small side table.

2. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A compact kitchen with a dining table, a refrigerator, and a trash can.

3. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is £308
includes taxes & fees
22 Oct - 23 Oct
Spacious Apt | 4 Queen Beds | Free Parking
Private kitchen

4. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is £173
includes taxes & fees
20 Oct - 21 Oct
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern living room with a blue sofa, a patterned rug, and a television.

5. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is £163
includes taxes & fees
13 Oct - 14 Oct
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern living room with a grey sofa, a coffee table, and a view of the outside through large windows.

6. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
The price is £193
includes taxes & fees
7 Oct - 8 Oct
Conveniently Situated 1BR Apartment
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

7. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is £178
includes taxes & fees
28 Oct - 29 Oct
The Oak Park Loft
A modern living room with a sofa, a round coffee table, a TV mounted on the wall, and a bed with a headboard.

8. Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time at this property! After our previous rental cancelled at the last minute, we found this gem and couldn’t have been happier. Communication was clear, check-in was easy, and the property was clean and comfortable. Thanks for a great stay!"
United States
Emily G.
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

9. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is £150
includes taxes & fees
12 Oct - 13 Oct
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

10. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Great place to stay "
United States
Harquesha S.
The price is £139
includes taxes & fees
13 Oct - 14 Oct
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

11. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is £235
includes taxes & fees
27 Oct - 28 Oct
2BR Apt with 2 Baths & Laundry
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

12. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is £240
includes taxes & fees
26 Oct - 27 Oct
Sleeps 7 • Huge Projector • Designated Workspace
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

13. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is £215
includes taxes & fees
15 Oct - 16 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

14. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (33 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is £139
includes taxes & fees
14 Oct - 15 Oct
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A modern bedroom with a bed, a sofa, and a hanging plant.

15. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (100 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is £108
includes taxes & fees
26 Oct - 27 Oct
Cozy studio in Andersonville Chicago
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

16. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is £315
includes taxes & fees
7 Oct - 8 Oct
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Terrace/patio

17. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is £250
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A living room with a grey sofa, a white coffee table, and a grey rug.

18. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (25 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
The price is £182
includes taxes & fees
2 Nov - 3 Nov
Small hidden Gem. Location!
A rooftop terrace with a brick wall, large windows, and a metal railing.

19. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is £271
includes taxes & fees
12 Oct - 13 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Private kitchen

20. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
The price is £198
includes taxes & fees
27 Oct - 28 Oct
1BR Apartment - Walk to Shops - Downtown OAK PARK
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southwest Side Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Wonderful experience. So close to the river walk and activities. Staff was so helpful and attentive and property was clean and comfy! Highly recommend!"
Susan 4-night trip
Posted 1 hour ago
River Hotel

Find out more about Southwest Side

Southwest Side Apartments information

Number of reviews
377
Accommodation
639 Apartments
Lowest Price
£108
Highest Price
£315

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